Bis-Schiff base compositions and formulations

ABSTRACT

Chemical compositions are provided having the structure of Formula (I): 
                         
where R includes at least one aromatic moiety, and X and X′ may both or independently include an aromatic moiety, an aliphatic moiety, or a hydrogen. Additionally, chemical formulations are provided which include the chemical composition having the structure of Formula (I) and at least one solvent.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. Non-Provisionalapplication Ser. No. 15/440,829, filed Feb. 23, 2017 which claims thebenefit of U.S. Provisional Application 62/298,504, filed Feb. 23, 2016,both of which are incorporated by reference herein in their entirety.

FIELD OF INVENTION

Embodiments of the present disclosure generally relate to bis-Schiffbase compositions and chemical formulations that include a bis-Schiffbase composition and a solvent. More specifically, embodiments of thepresent disclosure relate to bis-Schiff base compositions andformulations with improved melt viscosity and stability.

BACKGROUND

Schiff bases, named after Nobel Prize winner Hugo Schiff, are compoundshaving the general structure R₂C═NR′. A bis-Schiff base refers to acompound having at least two Schiff base components in the compound.Schiff bases are known to be useful intermediates in making catalysts,dyes, and polymers for wide variety of photo-chemical, electronic,opto-electronic, and photonic applications.

Conventional chemical processes to make bis-Schiff base compositions,such as bis-Schiff resins or its related polymer products, involve largequantities of organic solvent during synthesis and often require the useof catalysts and/or other polymerizable functional groups. Moreover, theprocesses often have multiple steps and laborious purificationprocesses. Bis-Schiff bases having epoxy functionalities may requireadditional curing agents and mixing processes to properly cure. As such,Schiff bases are not typically economically viable as a resin productfor the large-scale production of polymers or polymer composites.

Additionally, bis-Schiff bases of aliphatic aldehydes are readilypolymerizable and unstable. Bis-Schiff bases of aromatic aldehydes andaromatic amines are more stable, but more difficult to process,particularly for those with polyaromatic moieties, due to their highermelting points. When bis-Schiff base compositions are used as liquidresins, for instance, in molding or coating processes, the compositionsmust have viscosities that are malleable enough to manipulate.Typically, the composition would be heated until the appropriateviscosity was achieved, and the resin would be applied on a mold or asubstrate. However, conventional bis-Schiff bases may begin to undergofurther reactions, polymerizing and/or crosslinking when in a meltedstate due to their high melting point. This results in rapid increasesin viscosity and gelation that prevent the resin from being processedinto the desirable product form and shape.

SUMMARY

Accordingly, a need exists for bis-Schiff compositions with improvedrheology, such as a sufficiently low melt viscosity, that remainrelatively stable within a workable time and temperature processingwindow to allow the resin to be processed into a product form withoutfurther undesirable reactions occurring.

The present embodiments address these needs by providing chemicalcompositions, polymers produced from the chemical compositions, andchemical formulations with a much larger time and temperature processingwindow with desirably low viscosities. As used herein, “melt viscosity”refers to the measurement of the flow of a melted material, which may bemeasured based on the resistance to deformation as a function of shearrate or stress with dependence on time and temperature.

Embodiments of the present disclosure relate to chemical compositionshaving the structure of Formula (I):

where R comprises at least one aromatic moiety, and X and X′ may both orindependently comprise aromatic moieties, aliphatic moieties, or ahydrogen. The chemical composition may be a neat polymerizable resin. Asused herein, a “neat resin” refers to a resin that contains only themain identified monomers or polymers with minimal amounts or withoutstabilizers or additives.

Further embodiments of the present disclosure relate to polymersproduced from the chemical composition having the structure of Formula(I):

where R comprises at least one aromatic moiety, and X and X′ may both orindependently comprise aromatic moieties, aliphatic moieties, or ahydrogen.

Additional embodiments of the present disclosure relate to chemicalformulations having a component having the structure of Formula (I):

wherein R comprises at least one aromatic moiety, and X and X′ may bothor independently comprise aromatic moieties, aliphatic moieties, or ahydrogen; and at least one solvent.

BRIEF DESCRIPTION OF THE DRAWINGS

The following detailed description of specific embodiments of thepresent disclosure can be best understood when read in conjunction withthe following drawings, in which:

FIG. 1 is a nuclear magnetic resonance (NMR) spectroscopy spectrum of achemical composition according to the embodiments shown and describedherein;

FIG. 2 is an NMR spectrum of another embodiment of a chemicalcomposition according to the embodiments shown and described herein;

FIG. 3A is a viscosity versus temperature graph depicting the meltviscosity of an embodiment of a chemical composition according toembodiments shown and described herein;

FIG. 3B is a viscosity versus time and temperature graph depicting thestability of an embodiment of a chemical composition according toembodiments shown and described herein;

FIG. 4A is a viscosity versus temperature graph depicting the meltviscosity of another embodiment of a chemical composition according toembodiments shown and described herein; and

FIG. 4B is a viscosity versus time and temperature graph depicting thestability of an embodiment of a chemical composition according toembodiments shown and described herein.

DETAILED DESCRIPTION

Embodiments of the present disclosure generally relate to bis-Schiffbases. Specifically, embodiments of the present disclosure relate tochemical compositions, polymers produced from the chemical compositions,and chemical formulations, which comprise the structure of Formula (I):

where R is an aromatic moiety, and X and X′ may both or independentlycomprise aromatic, aliphatic moieties, or a hydrogen. The aromaticmoiety may be any suitable constituent containing a cyclic, ring-shapedfunctional group. The aliphatic moiety may be any saturated orunsaturated, straight or branched open-chain compound. In someembodiments, X, X′, or both X and X′ may be a hydrogen atom.

Any suitable aromatic moiety may be chosen for R, which may vary basedon the desired application of use. In some embodiments, R may contain atleast one of a phenyl group, a naphthyl group, an ether group, a sulfurgroup, a sulfonyl group, an imine group, an amide group, a methylenegroup, a dialkyl methylene group, an isopropyl group, a trifluoromethylgroup, a hexafluoroisopropyl group, a carbonyl group, a benzyl group, orcombinations of these. In some embodiments, R may be an aromatic moietyhaving the structure of at least one of Formula (II) or Formula (III):

where R′ and R″ may be, for instance, an oxygen group, an imine group,an amide group, a methylene group, a dialkyl methylene group, anisopropyl group, a trifluoromethyl group, a hexafluoroisopropyl group,an ether group, a sulfonyl group, a sulfur group.

It should be understood that a “group” is used to refer to a moietycontaining at least one atom. For instance, an “oxygen group” is used torefer to any moiety containing oxygen, such as a single oxygen atom or acomplex arrangement containing one or many oxygen atoms. In any of theformulas depicted throughout this disclosure, an unconnected bond “—X”refers to an open covalent bond, which may be a single, double, or evena triple bond between that constituent and another molecule.

In some embodiments, R may contain one or more of Formula (IV), Formula(V), Formula (VI), Formula (VII), Formula (VIII), Formula (IX), Formula(X), Formula (XI), Formula (XII), Formula (XIII), Formula (XIV), Formula(XV), Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX),Formula (XX), Formula (XXI), Formula (XXII), Formula (XXIII), Formula(XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII), Formula(XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI):

In one or more embodiments, for Formula (XXV), Formula (XXVI), Formula(XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula(XXXI), R₁, R₂, R₃, R₄, R₅, R₆, R₇, and R₈ are each independentlyselected from Formula (IV), Formula (V), Formula (VI), Formula (VII),Formula (VIII), Formula (IX), Formula (X), Formula (XI), Formula (XII),Formula (XIII), Formula (XIV), Formula (XV), Formula (XVI), Formula(XVII), Formula (XVIII), Formula (XIX), Formula (XX), Formula (XXI),Formula (XXII), Formula (XXIII), and Formula (XXIV), and the aromaticmoieties Ar₁, Ar₂, Ar₃, Ar₄, Ar₅, Ar₆, and Ar₇ may be meta-substitutedor para-substituted. It is noted that Formula (XXVIII), Formula (XXIX),Formula (XXX), and Formula (XXXI) are illustrated in broken form forclarity with the broken bonds represented by a tilde across the bond.

In some embodiments, the chemical composition may be a neatpolymerizable resin. In some embodiments, the chemical composition maycontain a monomer having the structure of Formula (I) with less than orequal to 5 wt % of fillers, reinforcements, pigments stabilizers, oradditives, based on the total weight of the resin. In some embodiments,the chemical composition may contain only a monomer having the structureof Formula (I) with less than or equal to 3 wt %, less than 2 wt %, orless than 1 wt % of fillers, reinforcements, pigments stabilizers, oradditives, based on the total weight of the resin. In some embodiments,the chemical composition may not contain, or may not contain more thantrace amounts of fillers, reinforcements, pigments stabilizers, oradditives.

In some embodiments, the chemical composition may be produced byreacting an aromatic diamine with a heterocyclic compound having atleast one carbonyl moiety. The carbonyl moiety may be an aldehyde or aketone functional group. In some embodiments, the structure of theheterocyclic compound may comprise Formula (XXXIII).

where X and X′ may both or independently comprise aromatic moieties,aliphatic moieties, or a hydrogen. In some particular embodiments, X maycomprise an aromatic or aliphatic moiety and X′ may be a hydrogen. Insome particular embodiments, X may comprise a methyl, a propyl, adimethylamino, boronic acid, a naphthyl, a phenyl, a 4-cyanophenyl, a(1-(5-(1-(5-Formyl-2-furfyl)-1-methylethyl)-2-furfyl)-1-methylethyl)moiety, or combinations thereof, and X′ may be a methyl group or ahydrogen.

Without being bound by any particular theory, the amine groups of thearomatic diamine may react with the heterocyclic compound, or with theheterocyclic compound and other aromatic dialdehyde compound, to producea bis-Schiff base compound having two heterocyclic moieties bonded atopposite ends of the structure through the two Schiff-base moieties, asdepicted in Formula (I).

In some particular embodiments, the heterocyclic compound may includefurfural, 5-methylfurfural,5-(1-(5-(1-(5-Formyl-2-furfyl)-1-methylethyl)-2-furfyl)-1-methylethyl)-2-furaldehyde,5-Propyl-furan-2-carbaldehyde, 5-(Dimethylamino)-2-furaldehyde,5-Formyl-2-furanylboronic acid, 5-(1-naphthyl)-2-furaldehyde,4-(5-formyl-furan-2-yl)benzonitrile, 3-Furancarboxaldehyde, orcombinations thereof.

The aromatic diamine may include at least one phenyl group, ether group,sulfonyl group, hydrocarbyl group, or combinations thereof. In someembodiments, the aromatic diamine may comprises the formula: NH₂—R³—NH₂in which R³ includes one or more of Formula (IV), Formula (V), Formula(VI), Formula (VII), Formula (VIII), Formula (IX), Formula (X), Formula(XI), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV),Formula (XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula(XX), Formula (XXI), Formula (XXII), or Formula (XXIII), as previouslydescribed. For instance, aromatic diamine, NH₂—R³—NH₂, may include4,4′-(1,3-phenylenedioxy)dianiline, 1,3-bis(3-aminophenoxy)benzene,4,4′-oxydianiline, 4-aminophenyl sulfone, 3-aminophenyl sulfone,isophthalaldehyde derivatives, or combinations thereof.

Without being bound by any particular theory, the chemical compositionmay have improved rheological properties, such as, for instance,viscosity stability and melt viscosity. In some embodiments, thechemical composition may have a viscosity of less than or equal to100,000 centipoises (cP) (i.e., 100 Pascal-seconds (Pa-s)) attemperatures of from 60° C. to 150° C. for at least 4 hours. Thechemical composition may have a melt viscosity that is relatively stablebetween 60° C. and 170° C., which may indicate that the chemicalcomposition is not curing or crosslinking or has a very slow curing ratebelow 170° C. In some embodiments, the chemical composition may have aviscosity of less than or equal to 100,000 cP at temperatures of from100° C. to 150° C., from 100° C. to 120° C., from 120° C. to 150° C.,from 60° C. to 170° C., or from 60° C. to 120° C. for at least 4 hours,for at least 3 hours, for at least 2 hours, for at least 1 hour, for atleast 5 hours, or for at least 6 hours. For instance, in someembodiments, the chemical composition may have a viscosity of between100 cP and 750 cP for at least 4 hours at 120° C. The chemicalcomposition may have a viscosity of between 100 cP and 750 cP, 250 cPand 600 cP, or 300 cP and 500 cP for at least 4 hours at 120° C. In someembodiments, the chemical composition may have a melt viscosity of lessthan or equal to 100,000 cP at less than or equal to 150° C., asmeasured by rotation rheometry. In some particular embodiments, thechemical composition may even have a melt viscosity of less than orequal to 500 cP at less than or equal to 150° C., as measured byrotation rheometry.

Again, without being bound by any particular theory, this may allow forat least 4 hours at which the chemical composition has a workableviscosity without undergoing gelation or otherwise further reacting,which may cause the composition to become un-processable. This maycreate a greater processing window (both in terms of time andtemperature) upon which the chemical composition is malleable and maybe, for instance, processed into a polymer or polymer composite. Thereaction rate of the further reactions, such as polymerization,crosslinking, and/or curing, may occur at a slower rate thanconventional resins.

In some embodiments, the chemical composition may have a low viscosity,such as below about 100,000 cP at temperatures below 170° C. Theviscosity may be measured by rotational rheometry by acquiring viscosityversus temperature curves on a parallel plate rheometer, commerciallyavailable from TA Instruments (New Castle, Del.) at a controlled strainof 0.01% and an angular frequency of 10.00 radians per second (rad/s) byheating samples at a rate of 2° C. per minute to the isothermaltemperature specified. In one or more embodiments, the chemicalcomposition may have a melt viscosity of less than or equal to 500 cP at125° C. as measured by rotation rheometry. In one or more embodiments,the chemical composition may have a melt viscosity of less than or equalto 100,000 cP at 125° C. as measured by rotation rheometry. Forinstance, the chemical composition may have a melt viscosity of from10,000 to 100,000 cP, from 40,000 to 80,000 cP, or from 20,000 to 50,000cP at 125° C. In some particular embodiments, the chemical compositionmay have an extremely low viscosity at less than 200° C., such as lessthan 500 cP. In some particular embodiments, the chemical compositionmay have a melt viscosity of from 100 to 500 cP, from 200 to 400 cP, orfrom 300 to 500 cP at 125° C.

Embodiments of the disclosure additionally relate to chemicalformulations produced by dissolving the chemical composition in at leastone solvent. In certain applications, such as using the chemicalcomposition as a material to produce thin film or coating on a panel orfabric, it may be advantageous to add solvent to the chemicalcomposition to dilute the solution before applying the chemicalcomposition via a coating or spray painting process to facilitate fastdrying of the resulting film or coating. In some instances, the additionof solvent to the chemical composition can impart desirable properties,such as a tackiness or a plasticizing effect, to the chemicalcomposition in order to make certain type of products, for instance apolymer composite prepreg. The chemical composition may be in accordancewith any of the embodiments previously described. Dissolution mayinclude any suitable techniques known in the art, including but notlimited to mixing, stirring, or otherwise agitating the formulation,with or without the application of heat.

Many solvents may be suitable for use in the chemical formulation. Thesolvent may be any substance that allows the chemical composition tobecome incorporated into the solvent as a solute. The solvent may, insome embodiments, be used to achieve a particular viscosity based on thedesired application of use. In some embodiments, the solvent may betoluene, dichloromethane, chloroform, acetone, tetrahydrofuran,cyclopentanone, parachlorobenzotrifluoride, dibasic ester,N-methylpyrrolidine, and combinations thereof. In some particularembodiments, the solvent may contain parachlorobenzotrifluoride. In someembodiments, parachlorobenzotrifluoride may be used to providesolubility without the use of volatile organic compounds (VOCs), whichcan pose environmental and health hazards.

Various amounts of the solvent are contemplated based on numerousfactors, such as, for instance, the solubility of the chemicalcomposition in the solvent and the relative strength of the solvent. Thestrength of the solvent may be determined based on the relative polarityof the solvent with respect to the chemical composition, which isrelated to the interaction of the composition with a solvent leading tothe stabilization of the chemical composition in solution. In someembodiments, the chemical formulation may contain from 10 weight percent(wt %) to 90 wt % of the chemical composition, as measured based on thetotal weight of the chemical formulation. The chemical formulation maycontain from 20 wt % to 90 wt %, 30 wt % to 90 wt %, from 40 wt % to 90wt %, from 50 wt % to 90 wt %, from 60 wt % to 90 wt %, or from 70 wt %to 90 wt % of the chemical composition. In some embodiments, thechemical formulation may contain from 30 wt % to 85 wt %, from 40 wt %to 60 wt %, from 30 wt % to 50 wt %, from 40 wt % to 70 wt %, or from 50wt % to 85 wt % of the chemical composition based on the total weight ofthe chemical formulation.

In some embodiments, the chemical formulation may contain a ratio of 1part of the chemical composition to 2 parts of solvent, or a 1:2 ratio.In other embodiments, the chemical formulation may contain from a 1:2 toa 1:10 ratio, such as from a 1:2 to a 1:5 ratio, a 1:2 to a 1:4 ratio,or a 1:2 to 1:3 ratio. In some embodiments, particularly in which thesolvent is strong, the chemical formulation may contain from a 10:1 to a1:2 ratio, such as from a 10:1 to a 1:1 ratio, from a 10:1 to a 5:1ratio, from a 10:1 to a 4:1 ratio, from a 2:1 to 3:1 ratio, or from a10:1 to 8:1 of chemical composition to solvent.

In some embodiments, the chemical composition, the chemical formulation,or both, may be used to produce a polymer or a polymer composite. As anon-limiting example, a chemical composition in which R is in accordancewith Formula (VII) may be thermally polymerized in a mold at 220° C. for4 hours to produce a thermosetting polymer that has a glass transitiontemperature of 154° C. with a storage modulus of 3.1 gigapascals (GPa)at room temperature.

In some embodiments, the polymer composite may be a fiber reinforcedcomposite, or it may be a particulate-reinforced composite. The chemicalcomposition, and its resulting polymer or polymer composite may be usedor may be formulated for use in many industries. For example, thecomposite may be used in the architecture, construction, oil and gas,mining, space, aerospace, defense, automotive, marine, or manufacturingindustries. In other embodiments, the chemical composition, and itsresulting polymer or polymer composite may be used in chemical, coating,pharmaceutical, apparel, or electronic industries.

The polymer produced from the present disclosure of chemical compositionmay, in some embodiments, not only have improved thermal and electronicqualities, and may also have advantageous mechanical properties as well.In some embodiments, the polymer may have a storage modulus of greaterthan or equal to 2 GPa, as measured according to the American Societyfor Testing and Materials (ASTM) Standard D4065. For instance, thepolymer may have a storage modulus of from 2 to 4 GPa, such as from 1 to3 GPa, or from 2 to 3 GPa, or from 3 to 4 GPa. In one or moreembodiments, due in part to the tailorability in the density of thecrosslinkable components within the chemical composition, the polymer orthe polymer composite made from it may be tailored to include a moreflexible polymer backbone component, thus allowing the resulting polymermaterial to have unique elastomeric and/or shape memory polymerproperties.

In some embodiments, due in part to these improved properties, thechemical composition, may be useful in a variety of industrialapplications. In some embodiments, the chemical composition the polymeror the polymer composite made from it, or both, may be used in thearchitecture, coating, composite, construction, oil and gas, mining,defense, space, aerospace, automotive, marine, manufacturing,pharmaceutical, or electronic industries. In some particularembodiments, the chemical composition, or the polymer made from it maybe used as chelating agents for use in chemical sensors to detectpresence of metal ions in solutions, such as Ag(II), Cu(II), Fe(II) orZn(II), Co(II), Hg(II), Ni(II), Pb(II), due to their abilities to formion complexes with these ions. In another embodiment, the chemicalcomposition or the polymer made from it, may be used in the making ofcatalyst for chemical synthesis by complexing with metal ions, such asAg(II), Cu(II), Fe(II) or Zn(II).

In other embodiments, the chemical composition, or the polymer made fromit, may be used to produce antifungal, antibacterial or antiviral agentsin pharmaceutical industry. In other embodiments, the chemicalcomposition, with or without solvent, or the polymer made from it, maybe used in the clothing industry to treat fabric, apparel to provideantifungal, antibacterial or antiviral properties. In other embodiments,the chemical composition or the polymer made from it, may be used asanti-corrosion agents due to the presence of the imine group, to preventcorrosion of metals such as steel, copper, aluminum, and zinc In otherembodiments, the chemical composition, the polymer made from it, orboth, may be used in electronic industries, for instance, in opticalcomputers, imaging systems, organic or lithium batteries, asphotostabilizers, optical memory storage, circuit board substrate, andas housing materials for electronic devices. In some other particularembodiments, the chemical composition may be used in making of neatpolymer, fiber-reinforced polymer composite, or particulate-reinforcedpolymer composite panel, parts, or structures for architecture, buildingconstruction, coating, composite, mining, oil and gas, space, aerospace,automotive, marine industries.

Examples

The various embodiments of the chemical compositions, formulations, andcomposites will be further clarified by the following examples. Theexamples are illustrative in nature, and should not be understood tolimit the subject matter of the present disclosure. To furtherillustrate the chemical properties of the chemical compositions andformulations of the present embodiments, experimental data was obtainedon two particular embodiments of the chemical compositions of thepresent disclosure.

Referring now to the Figures, FIG. 1 is a nuclear magnetic resonance(NMR) spectroscopy spectrum of one embodiment of the chemicalcomposition, Example 1. Example 1 is a chemical composition having theformula: C₂₈H₂₀N₂O₄, where R is in accordance with Formula VII. Thechemical structure of Example 1 is:

Example 1 was prepared by equipping a 2 liter (L) three-neck flask witha mechanical stirrer and charging the center neck with 408.6 grams (g)of furfural. One neck was sealed with a septum and the mixer was set to200 rotations per minute (RPMs) and 603.4 g of4,4′-(1,3-Phenylenedioxy)dianiline was added through the remaining neck.The addition took place over a span of 20 minutes, after which theremaining neck was sealed with a septum. Upon the dissolution of thesolid material, the flask was heated to 100° C. using an oil bath andmixing was allowed to continue for 1 hour. A vacuum adaptor was attachedto one neck of the reaction vessel and the water produced by thereaction was removed in vacuo. The desired material was cooled andcharacterized by gas chromatography-mass spectrometry (GC/MS) and protonnuclear magnetic resonance spectroscopy (H NMR). Example 1 obtained ayield of greater than 90%.

The NMR spectrum details are as follows: ¹H NMR (82 MHz, CDCl₃) δ 8.24(s, 2H), 7.54 (d, J=1.8 Hz, 2H), 7.22 (dt, J=7.3, 2.7 Hz, 5H), 7.05 (d,J=2.4 Hz, 3H), 6.90 (d, J=3.5 Hz, 2H), 6.74 (m, 4H), 6.48 (dd, J=3.5,1.8 Hz, 2H). Mass Spectrum Calc. 448.4 Found 448.4. The above dataconfirms the structure of the compound.

Without being bound by any particular theory, the physical properties ofa polyphenyl ether (PPE), such as the chemical composition show inExample 1, may depend on the number of aromatic rings and thesubstitution pattern of those rings. PPEs that contain two and threebenzene rings are typically solids at room temperature. The meltingpoint however may be lowered if the PPE contains more meta-phenylenerings. Again, without being bound by any particular theory, it isbelieved the meta-substitution may lead to lower melting points or lowerviscosities at the same temperature as compared to para-substitutedcompounds. Typically, PPEs with ortho- and para-substituted rings havethe highest melting points.

FIG. 2 is another NMR spectrum of another embodiment of the chemicalcomposition having the formula C₂H₂₀N₂O₄, in which R comprises astructure according to Formula VI. The chemical structure of Example 2is:

Example 2 was prepared by equipping a 2 L three-neck flask with amechanical stirrer and charging the center neck with 408.6 g offurfural. One neck was sealed with a septum and the mixer was set to 200RPMs and 603.4 g of 1,3-Bis(3-aminophenoxy)benzene was added through theremaining neck. The addition took place over a span of 20 minutes, afterwhich the remaining neck was sealed with a septum. Upon the dissolutionof the solid material, the flask was heated to 100° C. using an oil bathand mixing was allowed to continue for 1 hour. A vacuum adaptor wasattached to one neck of the reaction vessel and the water produced bythe reaction was removed in vacuo. The desired material was cooled andcharacterized by GC/MS and ¹H NMR. Example 2 obtained a yield of greaterthan 90%.

The NMR spectrum details are as follows: ¹H NMR (82 MHz, CDCl₃) δ 8.25(s, 2H), 7.54 (d, J=1.8 Hz, 2H), 7.13 (tdd, J=8.9, 5.7, 2.3 Hz, 8H),6.90 (d, J=3.5 Hz, 2H), 6.74 (m, 4H), 6.48 (dd, J=3.5, 1.8 Hz, 2H). MassSpectrum Calc. 448.4 Found 448.4. This confirms the structure of thecompound. As previously mentioned, it is believed the meta-substitutionmay lead to lower melting points or lower viscosities at the sametemperature as compared to para-substituted compounds.

FIG. 3A is a graph of the viscosity versus temperature depicting themelt flow viscosity of a chemical composition in accordance with thepresent embodiments, Example 1. In FIG. 3A, Example 1 was heated at atemperature ramp of 2° C. per minute using a TA instrument parallelplate rheometer at a controlled strain of 0.01% and an angular frequencyof 10.00 rad/s. As shown in FIG. 3A, Example 1 exhibited a large drop inviscosity between room temperature and 100° C. as the composition melts,which levels and stabilizes between 150° C. and 200° C., indicating thatthe composition is not curing below 200° C. (rapid rising would indicatethe composition is curing or otherwise further reacting). FIG. 3A alsoshows that Example 1 had a low viscosity over a large temperature rangeof up to a temperature of at least 200° C., leaving an ample temperatureprocessing window in which Example 1 had a viscosity of about less than1000 cP (1 Pa s).

FIG. 3B is another graph of viscosity versus temperature and time,showing the stability of the chemical composition of Example 1. Theviscosity versus temperature curves were acquired on a TA instrumentsparallel plate rheometer at a controlled strain of 0.01% and an angularfrequency of 10.00 rad/s. Samples were heated at a rate or 2° C. perminute to the isothermal temperature of 120° C. FIG. 3B shows Example 1during a 4 hour dwell at 120° C. As shown, Example 1 was stable between150 cP to 200 cP for a period of time of at least 4 hours. Example 1 wasable to maintain a low melt flow viscosity for long periods withoutundergoing further reactions or showing signs of a significant increasein viscosity or temperature. This may allow for an extremely desirableworking processing window or “pot life” in which Example 1 may be usedin a variety of composite fabrication processes due to the improvedworkability, handling, and processing caused by the low viscosity over along time period.

Similarly, FIG. 4A is another viscosity versus temperature graph of achemical composition in accordance with the present embodiments, Example2. In FIG. 4A, Example 2 was again heated at a temperature ramp of 2° C.per minute. Like Example 1, Example 2 has a large drop in viscositybetween room temperature and 100° C., which levels between 150° C. and200° C., indicating that the composition did not exhibit significantcuring below 200° C. within the experimental time frame. Again, Example2 exhibits low viscosity over a large temperature range of up to atemperature of at least 200° C., leaving an ample temperature processingwindow (from at least about 100° C. to 200° C.) in which Example 2 had aviscosity of about less than 1000 cP.

FIG. 4B is another viscosity versus temperature and time graph showingthe stability of the chemical composition of Example 2. FIG. 4B showsExample 2 during a 4 hour dwell at 120° C. Again, Example 2 was stablebetween 150 cP and 200 cP for at least 4 hours. Example 2 was able tomaintain a low melt flow viscosity without undergoing further reactionsor showing signs of either a significant increase in viscosity or intemperature, showing improved workability over a range of up to at least4 hours.

It should be apparent to those skilled in the art that variousmodifications and variations may be made to the embodiments describedwithin without departing from the spirit and scope of the claimedsubject matter. Thus, it is intended that the specification cover themodifications and variations of the various embodiments described withinprovided such modification and variations come within the scope of theappended claims and their equivalents.

As used throughout, the singular forms “a,” “an” and “the” includeplural referents unless the context clearly dictates otherwise. Thus,for example, reference to “a” component includes aspects having two ormore such components, unless the context clearly indicates otherwise.

Having described the subject matter of the present disclosure in detailand by reference to specific embodiments thereof, it is noted that thevarious details disclosed within should not be taken to imply that thesedetails relate to elements that are essential components of the variousembodiments described within, even in cases where a particular elementis illustrated in each of the drawings that accompany the presentdescription. Further, it should be apparent that modifications andvariations are possible without departing from the scope of the presentdisclosure, including, but not limited to, embodiments defined in theappended claims. More specifically, although some aspects of the presentdisclosure are identified as particularly advantageous, it iscontemplated that the present disclosure is not necessarily limited tothese aspects.

What is claimed is:
 1. A chemical composition comprising a chemicalhaving the structure of Formula (I):

wherein: R is selected from at least one of Formula (IV), Formula (V),Formula (VI), Formula (VII), Formula (IX), Formula (X), Formula (XI),Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula(XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX),Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula(XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula(XXX), or Formula (XXXI); X comprises an aromatic moiety, an aliphaticmoiety, or a hydrogen when R is selected from Formula (VI), Formula(VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV),Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula(XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI),Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), orFormula (XXXI); X consists of a hydrogen when R is selected from Formula(IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula(XVII); X′ comprises an aromatic moiety, an aliphatic moiety, or ahydrogen when R is selected from Formula (VI), Formula (VII), Formula(VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV),Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula(XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII),Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI); andX′ consists of a hydrogen when R is selected from Formula (IV), Formula(V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII):

wherein for Formula (XXV), Formula (XXVI), Formula (XXVII), Formula(XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI): R₁, R₂, R₃,R₄, R₅, R₆, R₇, and R₈ are each independently selected from Formula(IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula(IX), Formula (X), Formula (XI), Formula (XII), Formula (XIII), Formula(XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII),Formula (XIX), Formula (XX), Formula (XXI), Formula (XXII), Formula(XXIII), and Formula (XXIV), the aromatic moieties Ar₁, Ar₂, Ar₃, Ar₄,Ar₅, Ar₆, and Ar₇ are meta-substituted or para-substituted; and Formula(XXVIII), Formula (XXIX), Formula (XXX), and Formula (XXXI) are eachillustrated broken across multiple lines but represent a singlecontinuous structure.
 2. The chemical composition of claim 1, whereinthe chemical composition has a melt viscosity of less than or equal to500 cP at less than or equal to 150° C., as measured by rotationalrheometry.
 3. The chemical composition of claim 1, wherein the chemicalcomposition is used in at least one of an architecture, coating,composite, construction, oil and gas, mining, defense, space, aerospace,automotive, marine, or electronic industries.
 4. The chemicalcomposition of claim 3, wherein the chemical composition is used as athermosetting resin in the composite industry.
 5. The chemicalcomposition of claim 3, wherein the chemical composition is used as athermosetting resin in the coating industry.
 6. A polymer produced fromthe chemical composition of claim
 1. 7. The polymer of claim 6, whereinthe polymer is used in at least one of an architecture, coating,construction, oil and gas, mining, defense, space, aerospace,automotive, marine, manufacturing, or electronic industries.
 8. Thepolymer of claim 6, wherein the polymer is used as a thermosetting resinin the composite industry.
 9. The polymer of claim 6, wherein thepolymer is used as a thermosetting resin in the coating industry.
 10. Achemical formulation comprising: at least one solvent; and a chemicalhaving the structure of Formula (I):

wherein: R is selected from at least one of Formula (IV), Formula (V),Formula (VI), Formula (VII), Formula (IX), Formula (X), Formula (XI),Formula (XII), Formula (XIII), Formula (XIV), Formula (XV), Formula(XVI), Formula (XVII), Formula (XVIII), Formula (XIX), Formula (XX),Formula (XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula(XXVI), Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula(XXX), or Formula (XXXI); X comprises an aromatic moiety, an aliphaticmoiety, or a hydrogen when R is selected from Formula (VI), Formula(VII), Formula (VIII), Formula (XII), Formula (XIII), Formula (XIV),Formula (XV), Formula (XVI), Formula (XIX), Formula (XX), Formula(XXII), Formula (XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI),Formula (XXVII), Formula (XXVIII), Formula (XXIX), Formula (XXX), orFormula (XXXI); X consists of a hydrogen when R is selected from Formula(IV), Formula (V), Formula (IX), Formula (X), Formula (XI), or Formula(XVII); X′ comprises an aromatic moiety, an aliphatic moiety, or ahydrogen when R is selected from Formula (VI), Formula (VII), Formula(VIII), Formula (XII), Formula (XIII), Formula (XIV), Formula (XV),Formula (XVI), Formula (XIX), Formula (XX), Formula (XXII), Formula(XXIII), Formula (XXIV), Formula (XXV), Formula (XXVI), Formula (XXVII),Formula (XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI); andX′ consists of a hydrogen when R is selected from Formula (IV), Formula(V), Formula (IX), Formula (X), Formula (XI), or Formula (XVII):

wherein for Formula (XXV), Formula (XXVI), Formula (XXVII), Formula(XXVIII), Formula (XXIX), Formula (XXX), or Formula (XXXI): R₁, R₂, R₃,R₄, R₅, R₆, R₇, and R₈ are each independently selected from Formula(IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), Formula(IX), Formula (X), Formula (XI), Formula (XII), Formula (XIII), Formula(XIV), Formula (XV), Formula (XVI), Formula (XVII), Formula (XVIII),Formula (XIX), Formula (XX), Formula (XXI), Formula (XXII), Formula(XXIII), and Formula (XXIV), the aromatic moieties Ar₁, Ar₂, Ar₃, Ar₄,Ar₅, Ar₆, and Ar₇ are meta-substituted or para-substituted; and Formula(XXVIII), Formula (XXIX), Formula (XXX), and Formula (XXXI) are eachillustrated broken across multiple lines but represent a singlecontinuous structure.
 11. The chemical formulation of claim 10, whereinthe solvent is selected from the group consisting of toluene,dichloromethane, chloroform, acetone, tetrahydrofuran, cyclopentanone,parachlorobenzotrifluoride, dibasic ester, N-methylpyrrolidine, andcombinations thereof.
 12. The chemical formulation of claim 10, whereinthe chemical composition contains from 10 wt % to 90 wt % of thechemical having the structure of Formula (I).
 13. The chemicalformulation of claim 10, wherein the chemical composition contains from40 wt % to 85 wt % of the chemical having the structure of Formula (I).14. The chemical formulation of claim 10, wherein the formulation isused in at least one of an architecture, coating, construction, oil andgas, mining, defense, space, aerospace, automotive, marine,manufacturing, or electronic industries.